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Nitrogen heteroaromatic cations by [2+2+2] cycloaddition
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SYSNO ASEP 0363295 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Nitrogen heteroaromatic cations by [2+2+2] cycloaddition Author(s) Čížková, Martina (UOCHB-X) RID
Kolivoška, Viliam (UFCH-W) RID, ORCID
Císařová, I. (CZ)
Šaman, David (UOCHB-X) RID, ORCID
Pospíšil, Lubomír (UOCHB-X) RID, ORCID
Teplý, Filip (UOCHB-X) RID, ORCIDNumber of authors 6 Source Title Organic & Biomolecular Chemistry. - : Royal Society of Chemistry - ISSN 1477-0520
Roč. 9, č. 2 (2011), s. 450-462Number of pages 13 s. Language eng - English Country GB - United Kingdom Keywords modular synthesis ; N-heteroaromatic cation ; [2+2+2] cycloaddition Subject RIV CC - Organic Chemistry R&D Projects GA203/09/1614 GA ČR - Czech Science Foundation (CSF) GA203/09/0705 GA ČR - Czech Science Foundation (CSF) OC 140 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) CEZ AV0Z40550506 - UOCHB-X (2005-2011) AV0Z40400503 - UFCH-W (2005-2011) UT WOS 000285749800021 DOI 10.1039/c0ob00507j Annotation A modular approach to the construction of monocationic quaternary N-heteroaromatic frameworks was developed capitalizing on a direct pyridine-type nitrogen quaternization followed by metal-catalyzed [2+2+2] cycloaddition with gaseous acetylene. The flexibility of the route is demonstrated on 12 diverse scaffolds based on pyridinium, quinolinium, thiazolium, benzothiazolium, imidazolium, and pyrimidinium. Electrochemical study revealed a quinolinium redox system with two electrochemically distinct forms that are interconverted by a homogeneous chemical reaction triggered by fast electron transfers (reduction at -0.7 V and oxidation at -0.05 V). Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Year of Publishing 2012
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